Hans jordan



gen atoms have been fixed.

Patented Nov. 25, 1930 UNITED STATES .pAreNr oFE c HANS JORDAN, or isnnmn-s'rnemmz, GERMANY, assronoa To cirnivrrscnn rnnmx V AUF Acrmn vomvr. E. SCHEBINGLDFBERLIN,GERMANY a METHOD on PRODUCING PRODUCTS: or rrYnRoGEnATIon oFAiiKYIiA'rEn rniiivoiis Ho Drawing. Application filed Ju1y'12, 1926, $61ia1 No. 122,032, and in Germany July 4, 1925.

My invention refers to the production of products of hydrogenation of; alkylated phenols and more especially to the production of alkylated cyclo hexanols.

I have found thatlby treating a product of condensation of a ketone and a phenol hay ing the formula wherein R and R are alkyl of aryl radicals, with hydrogen in the presence of a catalyst in such manner that themolecule of the con-" roduct is split up at the point :.HOH V I Pre'ferablythe hydrogenation of the split products is continuedv until fourteen hydro- I have further found that the splitting and the hydrogenation ofthe split products A needing for instance as follows:

can be eifected in a particularly effective n an nor in the presence ofa nickel catalyst containing manganese, and. thatthe operatlon preferably carried out at and above a tem- Example '1 100 parts by weight of p-dihydroxydiphenyl dimethyl methane are treated at 170 C. with hydrogen under pressure in the presence reaction is, subjected to fractional distillaadvantages thereof.

Example j By treating, 4-dihydroXy 3-dimethy1'diphenyl di nethyl methane withhydrogen as I described with reference to Example 1, there are obtained l-inethyl cyclo hexan ol andl methyl-4-isopropyl cycloheirano'l,

Example 5" i By treating p-dihydroxydiphenyl methyl ethyl methane as described with reference to Example 1, there is obtainedt-isobutyl cyclo heXanol] and some cyclohexanol. p

' Various changes may be made in the details of theoperation and particularly in the proportions of the ingredients without departing from the invention or sacrificing the I claim 1. The method of producing products of hydrogenation of alkylated phenols, comprising subjecting aproduct of condensation of a ketoneand a phenol having the formula HO OH wherein R and R are alkyl or aryl radicals to treatment at a temperature of at least 170 7 1 C. with hydrogen in the presence of a mixed hydrogenation catalyst .in such manner that the molecule of the compound is split up at the point where the ketone connects the phenol radicals, and simultaneously hydrogenating the splitproducts further. I

2 The method of producing products of hydrogenation of alkylated phenols, compris ing subjecting a product of condensation ofa ketone' and ajphenol having the formula wherein R and R are alkyl or arylradicalsto treatment at a temperature of atleast :17 0 C.

With hydrogen in the presence of a mixed hydrogenation catalyst containing manganese in such manner that the molecule of the compound is split up at the point Where the ketone connects the phenol radicals, and simultaneously hydrogenating the split products further.

3. The methocl of producing products of hydrogenation of alkylated phenols, comprising subjecting a product of condensation of a ketone and a phenol having the formula wherein R and R are alkyl or aryl radicals to treatment at a temperature of at least 170 C. With hydrogen in the presence of a nickel catalyst containing manganese in such manner that the molecule of the compound is split up at the point Where the ketone connects the phenol radicals; and simultaneously hydrogenating the split products further.

4:. The method of producing isopropyl cyclo hexanol comprising treating 100 parts by Weight of p-dihydroXy diphenyl dimethyl methane in the presence of 2 parts of a nickel catalyst containing manganese at 170 C. with hydrogen under pressure, until fourteen hydrogen atoms have been fixed, and subjecting the product to fractional distillation.

In testimony whereof I affix my signature.

HANS JORDAN. 

